Our invention relates to pentamethyl indane derivatives, all derived from the hydrocarbon having the structure: ##STR2##
by means of first reacting such hydrocarbon with a mixture of carbon monoxide and hydrogen using an "oxo reaction catalyst" in order to form a carboxaldehyde having the structure: ##STR3##
or stereoisomers thereof. Such carboxaldehydes may then be used as is for their perfumery properties or may be reacted further, for example, by means of reduction, Grignard synthesis or the like. The resultant carboxaldehydes and resultant derivatives thereof have intense and substantive and aesthetically pleasing fragrance nuances and are thus useful in the formulation of fragrance compositions.
Velvety, diffusive, sweet, rich, warm, sensual, intense musky, floral, ambery, spicy, woody, balsamic, earthy, rooty and vetiver-like aromas with sensual, animalic, powdery, creamy, costus and musky topnotes and sweet, musky, spicy and floral undertones are particularly desirable in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and perfumed polymers).
Compounds having the oxygen-substituted pentamethyl indane structure and pentamethyl indane hydrocarbons are known for use in perfumery. Thus, U.S. Pat. No. 3,806,472 issued on Apr. 23, 1974 discloses the use in prefumery of the compound having the structure: ##STR4##
U.S. Pat. No. 3,636,165 issued on Jan. 18, 1972 discloses the perfumery utilities of the compounds having the structures: ##STR5##
U.S. Pat. No. 3,773,836 issued on Nov. 20, 1973 discloses the perfumery use of the compound having the structure: ##STR6##
U.S. Pat. No. 4,902,840 issued on Feb. 26, 1990 discloses the perfumery use of the compound having the structure: ##STR7##
The prior art does not, however, disclose the organoleptic utilities of compounds defined according to the structure: ##STR8## ##STR9##
wherein G' is one of the moieties: ##STR10##
wherein R.sub.6 and R.sub.7 are the same or different C.sub.1 -C.sub.3 lower alkyl and R.sub.1, R.sub.2, R.sub.4 and R.sub.5 are the same or different methyl or ethyl; and R.sub.3 is hydrogen or methyl with the provisos:
(i) when R.sub.3 is hydrogen, one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is ethyl and the other of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is methyl; and PA1 (ii) when R.sub.3 is methyl, then R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each methyl. PA1 (i) when R.sub.3 is hydrogen, one of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 is ethyl and the other is methyl; and PA1 (ii) when R.sub.3 is methyl, then one of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 is methyl; wherein R.sub.6 and R.sub.7 are the same or different C.sub.1 -C.sub.3 lower alkyl; and wherein X is chloro, bromo or iodo. PA1 (i) when R.sub.3 is hydrogen, one of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 is ethyl and the other is methyl; and PA1 (ii) when R.sub.3 is methyl, one of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 are each methyl.